Novel compositions of matter and processes of preparing same



United States Patent Ofitice 2,814,008 Patented Nov. 2a, 1957 NOVELCOMPOSITIONS OF MATTER AND PROCESSES OF PREPARING SAME John C.Petropoulos, South Norwalk, Conn., assignor to American CyanamidCompany, New York, N. Y., a corporation of Maine No Drawing. ApplicationMarch 2, 1955, Serial No. 491,770

20 Claims. (Cl. 260-72) This invention relates to novel condensationproducts and to the process of preparing the same. More particularly,this invention relates to the process of preparing condensation productsby reacting an aldehyde with certain sulfamoyl indans and to the productthus produced. Still further, this invention relates to the process ofreacting an aldehyde, a compound containing an alcoholic hydroxy groupand certain sulfamoyl indans and to the products thus produced.

One of the objects of the present invention is to produce a condensationproduct by reacting an aldehyde with sulfamoyl indans. A further objectof the present invention is to produce condensation products by reactingan aldehyde with a compound containing an alcoholic hydroxy group and acompound having the general formula:

R Rumors wherein R is a member selected from the group consisting of ahalo group and an alkyl group, containing from 1 to 4 carbon atoms, R isan alkyl group containing from 1 to 4 carbon atoms and R is a memberselected from the group consisting of H and an alkyl group containing 1to 20 carbon atoms. These and other objects of the present inventionwill be discussed in greater detail hereinbelow.

The sulfamoyl indanes used in the preparation of the condensationproducts of the present invention may be prepared by reacting ammoniawith the sulfonated reaction product of an indan derived from thedimerization of an alpha alkyl p-alkyl styrene and the like.

The sulfamoyl indanes used in the present invention may be prepared bystarting with dimers of substituted styrenes having an alkyl group or ahalo group in the alpha position and an alkyl group having between 1 and4 carbon atoms on the ring. The alkyl group in the alpha position may beany one of methyl, ethyl, propyl, and butyl. The same applies in thealkyl group on the ring. The alkyl group on the ring may be in eitherthe ortho, meta or para position. Representative of the class of alkylsubstituted styrenes which may be used in the practice of the process ofthe present invention are :,0-dimethylstyrene, m-dimethylstyrene,a,p-dimethylstyrene,

u,ethyl-o-methylstyrene, a-ethyl-m-methylstyrene, a-ethylsubstituted onthe side chain in the or position, one may utilize the halo substituentssuch as the chloro, bromo, iodo and fluoro. Representative of this classof compounds are a-chloro-m-methylstyrene, a-bromo-p-methylstyrene,a-iodo-o-methylstyrene, a-fluoro-p-methylstyrene and the like. The alkylsubstituent on the ring may be the sole substituent on the ring or itmay be accompanied by other substituents such as other alkyl groups,halo groups, such as those mentioned hereinabove and the like. Styrenesthat are unsubstituted on the ring may also be used. In order that theprocess for the preparation of these dimers may be more completelyunderstood, the following examples are set forth in which all parts areparts by weight unless otherwise indicated. These examples are set forthprimarily for the purpose of illustration and any specific enumerationof detail contained therein should not be interpreted as a limitation onthe case except as indicated in the appended claims.

DIMERIZATION OF oz,p-DIMETHYLSTYRENE 800 parts of toluene cooled to 5 C.are introduced into a suitable reaction vessel. To the toluene, there isadded 140 parts of a sulfuric acid. The mixture is stirred thoroughlyand maintained at a temperature of about 0-5 C. To the cooled mixture,there is added 260 parts of u,p-dimethylstyrene dissolved in 200 partsof toluene. The resulting mixture is allowed to react for /2 hour at 05C. and is then hydrolyzed with parts of water. The organic layer, iswashed free of acidic material, with water and is distilled to yield 250parts of a colorless oil having a boiling point of l42-144 C. at 0.8 mm.This oil solidifies and has a melting point of 3738 C. uncorrected.

DIMERIZATION OF a-ETHYL-p-METHYLSTYRENE To 400 parts of toluene at 5 0,there is added slowly 70 parts of 95% sulfuric acid followed by 144parts of ot-ethyl-p-methylstyrene dissolved in 100 parts of toluene. Thetemperature is maintained at 0-10" C. during the entire addition. Theresulting mixture is allowed to react for /2 hour and then is hydrolyzedwith 100 parts of water. The organic material is collected, washed freeof acidic material with water and distilled to yield parts of acolorless liquid having a boiling point of 160-165 C. at 1 mm.

DIMERIZATION OF a,META-DIMETHYLSTYRENE To 200 parts of toluene at 05 C.,there is added slowly 35 parts of 95% sulfuric acid, 65 parts of 0:,111-dimethylstyrene dissolved in 50 parts of toluene. The resulting mixtureis allowed to react for about hour and is then hydrolyzed with water.The organic material is collected, washed and distilled to yield 61parts of a colorless liquid having a boiling point of 144-148 C. at 1mm. pressure.

DIMERIZATION OF CRUDE a,p-DIMETHYL- STY-RENE To 368 parts of toluene at10 0., there is added slowly 50 parts of anhydrous aluminum chloridefollowed by 516 parts of crude (undistilled) a,p-dimethylstyrenedissolved in 368 parts of toluene while maintaining the temperaturebelow 10 C. After a 20-minute reaction time, the mixture is hydrolyzedwith water and the organic layer is collected and dried. The organicmaterial is distilled to give parts of a colorless oil having a boilingpoint of 138140 C. at 0.54 mm.

DIMERIZATION OF a,p-DIMETHYLSTYRENE A mixture of 310 parts of freshlydistilled u,p-dimethylstyrene and 2 parts of p-toluene sulfonic acid areheated in a steam bath for about 16 hours and then allowed to react atroom temperature for 2% months, at which time the p-toluene sulfonicacid catalyst is removed by washing the organic layer with dilute sodiumbicarbonate solution. Distillation of the organic layer gave 151 partsof a very light yellow colored oil having a boiling point of 136140 C.at 1 mm. pressure.

By dimerizing alpha alkyl styrenes of alpha halo styrenes in a mannercomparable to the example set forth hereinabove, one could produce thefollowing indanes which would be useful as a starting material in thepreparation of sulfamoyl derivatives used to form the condensationproducts of the present invention: 1-phenyl-1,3,3- trimethyl-indan;l-phenyl-l,3-diethyl-3-methyl-indan; 1-phenyl-1,3-dipropyl3-methyl-indan; l-phenyl-1,3-dibutyl- 3-methyl-indan;l-phenyl-1,3-dichloro-3-methyl-indan; 1-phenyl-l,3-diiodo-3-methyl-indan; 1-phenyl-1,3-dibromo- 3-methyl-indan;l-phenyl-1,3-difiuoro-3-methyl-indan; l-(4-methylphenyl)-1,3,3,6-tetramethyl-indan;1-(4-methylphenyl)-1,3-diethyl-3,6-dimethyl-indan; 1-(4-methylphenyl)-l,3-dipropyl-3,6-dimethyl-indan; 1-(4-methylphenyl)-l,3-dibutyl3,6-dimethyl-indan; 1-(3-methylphenyl)-l,3,3,-S-tetramethyl-indan; 1-(3-methylphenyl)-1,3-diethyl-3,5- dimethyl-indan;I-(S-methylphenyl)-1,3-dipropyl-3,5-dimethyl-indan; l-( 3-methylphenyl)-1,3-dibutyl-3,5-dimethyl-indan; 1-( 3-methylphenyl) -1,3-dichloro-3 ,5-dimethy1- indan; 1-(3-methylphenyl)-1,3-dibromo-3 ,5 -dimethyl-indanand the like.

In order to prepare the sulfamoyl derivatives from indanes such as thoseset forth hereinabove, it is necessary to prepare the sulfonatederivative as a starting material which sulfouate derivative may beconverted to the sulfarnoyl derivative by reaction with ammonia or byreacting the sulfonate derivative with an alkaline material to form thesalt of the sulfonate, thereafter reacting the said salt with a halogendonor to produce the sulfonyl halide which is then reacted with ammoniato produce the sulfamoyl derivative. Although the former process iseffective, the yields are comparatively small and, as a consequence, inview of the much larger yields the latter approach is more desirable. Inorder that this process may be completely understood, the followingexamples are set forth in which all parts are parts by weight. Theseexamples are set forth primarily for the purpose of illustration and anyspecific enumeration of detail contained therein should not beinterpreted as a limitation on the case except as is indicated in theappended claims.

METHOD FOR THE PREPARATION OF 1-(4-METH- YL 3 SULFAMOYLPHENYL) 1,3,3,6TETRA- METHYL-5-SULFAMOYL-INDAN Into a suitable reaction vessel equippedwith thermometer and stirrer, there is introduced 250 parts of l-(4-methylphenyl)-l,3,3,6-tetramethyl-indan. The charge is heated to about50 C. and there is slowly added 400 parts of fuming sulfuric acid (l8%).The reaction mixture is raised to about 100 C. at which time it iscooled and poured into a mixture of 1000 parts of concentratedhydrochloric acid and 500 parts of water. On cooling, needle-likecrystals appear and are collected. The disulfonic acid crystals thusproduced melt at about 100- 104 C. and have a neutral equivalent of 239indicating that the acid crystallizes with two molecules of water. 50parts of the acid are dissolved in 50 parts of water and to the solutionthere is added gradually a solution of potassium hydroxide until a pH of8 is reached. The salt solution thus produced is evaporated to drynesson a tray. A mixture of 18 parts of the anhydrous dipotassium salt ofthe acid thus produced and 18.5 parts of phosphorus pentachloride arestirred together in a suitable reaction vessel during the exotherm. Thepaste which is formed is heated after the exotherm at 110-120 C. forabout 1 hour. The volatiles (excess phosphorus pentachloride andphosphorus oxychloride is formed) are removed by vacuum concentration at100 C. for 1% hours. The solid product produced is ground to a powderousmaterial and mixed with parts of water and 100 parts of chloroform. Thechloroform layer is concentrated. Heptane is added to the concentratecausing the solid product to precipitate. The yield amounted to about91% and melted at -141 C. unc. Recrystallization from heptane raised themelting point to 1423 C. unc.

Into a suitable reaction vessel equipped with thermometer, stirrer andreflux condenser, there is added a mixture of 5 parts of disulfonylchloride compound thus produced and 50 parts of a 28% aqueous ammoniasolution and 1 part of chloroform. The mixture is heated on a steam bathfor one hour with constant stirring. The mixture is cooled in an icebath, and acidified to Congo-red with dilute sulfuric acid. The solidmaterial which forms is collected in a 97% yield and has a melting pointof 194- 7 C. unc. Recrystallization raises the melting point to 205 C.uncorrected and 240 C. uncorrected. The material is seeminglypolymorphic, it melts at 205 C., resolidifies at 210 C. and then remeltsat 240 C.

Analysis.Calculated for C20, H26, N2, 04, S2: C, 56.84; H, 6.20; N,6.63. Found: C, 56.67; H, 6.44; N, 6.4-2.

METHOD FOR THE PREPARATION OF 1-[4-METH- YL-3-(PROPYLSULFAMOYL)PHENYLl-1,3,3,6- TETRAMETHYL 5 PROPYLSULFAMOYL- INDAN Into a suitablereaction vessel equipped with thermometer, stirrer and refiux condenser,there is added 50 parts by weight of a 10% aqueous solution of potassiumhydroxide and 20 parts of n-propylamine. To this mixture, there is addedslowly 7 parts of the disulfonyl chloride compound prepared according tothe first part of the Example 1 Into a suitable reaction vessel equippedwith thermometer, stirrer and reflux condenser, there is introduced amixture of 10 parts of 1-(4-methyl-3-sulfamoyl-phenyl)-1,3,3,6-tetramethyl-5-sulfamoyl indan, 3.9 parts of butyl formcel (a 40%solution of formaldehyde in butanol), 15 parts of butanol and 10 partsof xylol. The charge is heated gradually to the reflux temperature(about 93 C.) and maintained at that temperature for about 1 hour. Someof the volatile material (about 16 parts) is removed by distillation.The product produced is a clear, colorless resin having a viscosity of Eon the Gardner- Holdt scale at 25 C. when measured on a 50% solidssolution of the resin in a 50/50 mixture of xylol/butanol. A film of theresin thus produced is drawn down on glass and baked for 30 minutes at300 F. The resultant cured film is hard and is not affected by xylol.

Example 2 30 parts of the aminoplast resin prepared according to Example1 and 59 parts of a short oil alkyd resin (60% solids) are thoroughlymixed and a film is drawn down therefrom and baked for 30 minutes at 300F. The film thus produced is transparent, hard and had excellentchemical resistance.

Example 3 Into a suitable reaction vessel equipped as in Example 1,there is introduced 262 parts of 1-[4-methyl-3(propyl'sulfamoyl)-phenyl]-1, 3,3,6-tetramethyl-5-propylsulfamoyl indan, 78parts of butyl formcel, 300 parts of butanol and 200 parts of xylol. Theprocedure of Example 1 is carried out in all details except that therefluxing period is 12 hours. Thereafter, 300 parts of volatiles areremoved by vacuum distillation. The clear water-white resins thusproduced are compatible with alkyd resins. These mixtures of the novelaminoplast resins of the present example with conventional alkyd resinswhen baked at normal baking schedules yield transparent,chemical-resistant films.

Amongst the sulfamoyl indanes which may be used to prepare thealdehyde-condensation products of the present invention are1-(3-sulfamoylphenyl)-l,3,3-trimethyl-5- sulfamoyl indan;l-(4-sulfamoylphenyl)-1,3,3-trimethyl- 6-sulfamoyl-indan;l-(3-sulfamoylphenyl)-1,3-diethyl-3- methyl-S-sulfamoybindan; 1-(3-sulfamoylphenyl) -1,3-di butyl-3-methyl-5-sulfamoyl-indan; 1-3-sulfamoylphenyl) 1,3-dichloro-3-m'ethyl-S-sulfamoyl-indan;1-(4-sulfamoylphenyl)-1,3-dipropyl-3-methyl-6-sulfamoyl-indan; 1-(3-methylsulfamoylphenyl) 1,3,3 trimethyl methylsulfamoyl-indan; 1-B-methylsulfamoylphenyl) l ,3-dibutyl-3 -methyl-5-methylsulfamoyl-indan;l- 3 -methylsulfamoylphenyl)-1,3-dibromo-3-methyl-5-methylsulfamoylindan; 1-(4-propylsulfamoylphenyl -l ,3 ,3-trimethyl-6- propylsulfamoyl-indan;l-(4-propylsulfamoylphenyl)-1,3dipropyl-3-methyl-6-propylsulfamoyl-indan; l-(4-propylsulfamoylphenyl)-1,3-diiodo-3-rnethyl-6-propylsulfamoylindan; 1-3-laurylsulfamoylphenyl) l ,3 ,3-trimethyl-5- laurylsulfamoyl-indan; 1-(3-laurylsulfamoylphenyl) -1,3-dibutyl-3-methyl-S-Iaurylsulfamoyl-indang 1-(3-laurylsulfamoylphenyl)1,3 dichloro 3 methyl 5 laurylsulfamoyl-indan; 1-3-stearylsulfamoylphenyl -l,3 ,3-trimethyl-S-stearylsulfamoyl-indan;l-(3-eicosylsulfamoylphenyl)-1,3,3-trimethyl-5-eicosylsulfamoyl-indan;1-(3- eicosylsulfamoylphenyl) 1,3 diethyl 3 methyl 5eicosylsulfamoyl-indan; 1- 3-eicosylsulfamoylphenyl) -l ,3diiodo-3-methyl-5-eicosylsulfamoyl-indan; 1-(4-methyl-3-sulfamoylphenyl) 1,3,3,6 tetramethyl 5 sulfamoyl indan;l-(4-methyl-3-sulfamoylphenyl)-l,3-dipropyl-3,6-dimethyl-S-sulfamoyl-indan;1-(4-methyl-3-sulfamoylphenyl)-1,3-dibutyl-3,6-dimethyl-5-sulfamoyl-indan;1-(4- methyl 3 sulfamoylphenyl) 1,3 dichloro 3,6dimethyl-S-sulfamoyl-indan; l-(4-butyl-3-sulfamoylphenyl)-6-butyl-1,3,3-trimethyl-5-sulfamoyl-indan; l-[4-propyl-3-(methylsulfamoyl) phenyl] 1,3,3 trimethyl 6 propyl-S-methylsu1fam'oyl-indan; 1- 4-propyl-3- butyls ulfamoyl) -phenyll -1, 3,3 -tributyl-6-propyl-5-butylsulfamoylindan; 1- 4-propyl-3-(hexylsulfamoyl) -phenyl]1,3,3-trimethyl-6-propyl-S-hexylsulfamoyl-indan; l-[4-propyl-3-(-decylsulfamoyl) phenyl] 1,3,3 trimethyl 6 propylS-decylsulfamoyl-indan; 1- [4-propyl-3- (hexadecylsulfamoyl) phenyl]1,3,3 trimethyl 6 propyl 5 hexadecylsulfamoyl-indan, and the like.

Amongst the aldehydes that may be used to form condensation productswith the sulfamoyl indanes of the present invention are formaldehyde,acetaldehyde, heptaldehyde, benzaldehyde, crotonic aldehyde, acrolein,furfural and the like. The term aldehydes includes not only thealdehydes themselves but also compounds engendering aldehydes; forinstance, p-formaldehyde, tetraethylene pentamine, trioxy methylene,p-aldehyde, and the like. Of these, formaldehyde is generally preferred.

Depending on the particular aldehyde selected and/or the ultimateresults desired, the reaction between the aldehyde and the sulfamoylindanes, the solvent medium, if any, can be aqueous or non-aqueous suchas organic solvents, either reactive or inert.

If it is desired to produce condensation products of aldehydes andsulfamoyl indanes that are ether derivatives, one may react the aldehydeand sulfamoyl indan in the presence of a compound containing analcoholic hydroxy group. As an alternative procedure, one may react thealdehyde with the sulfamoyl indan and thereafter react the condensationproduct with a compound containing an alcoholic hydroxy group. Amongstthese alcoholic compounds which may be used are the mono and polyhydricalcohols such as methanol, ethanol, butanol, ethyl butanol, ethylhexanol, lauryl alcohol, cetyl alcohol, stearyl alcohol, allyl alcohol,oleyl alcohol, glycol, glycerol, mannitol, sorbitol, benzyl alcohol,terpineol, borneol, abietineol, furfuryl alcohol and the like.

Among monoand polyhydric alcohols containing further substituents theremay be named ketoand aldehyde alcohols like aldol, glycol aldehyde,glycerol aldehyde; the groups of the carbohydrates, for example glucose,cane sugar, trihexosane or their polymerides, such as dextrine,starches, gum ,arabic, tragacanth or the like, oxycarboxylic acids, suchas tartaric acid, malic acid, ricinoleic acid, saccharic acid or theiresters or the like; halogen alkyl alcohols, for instance chlorethylalcohol, glycol chlorhydrin, glycerol chlorhydrin, chloralhydrate;amino-alcohols, for instance mono-, diand triethanolamine or the like.

Among the polyhydric alcohols those are of importance in which some ofthe oxy-groups have been etherified or esterified. Among these areglycolmonoethyl ether, glycolacetate, glycerolmonoand diethyl ether, forinstance diethyline, also cyclohexanone glycerol(Oot,0fi-cyclohexylidene-glycerol), glycerolmonoor di-esters, forexample those of saturated or unsaturated fatty acids. Also ester resinshaving free hydroxyl groups of the type of the alkyd resins may be used,for example the esters of glycerolphthalic acid ester, glycerol adipicacid ester or glycerol sebasic acid ester which still contain freehydroxyl groups.

Instead of the compounds containing alcoholic hydroxy groups themselvescompounds may be used which are converted under the conditions of thereaction into others containing alcoholic hydroxyl groups, for exampleacetals, esters.

Particularly advantageous for the invention are those of theabove-mentioned groups which are of the type of carbohydrates andbecause of their easy accessibility in nature.

The bodies which are to react may be brought together. simultaneously orin any order of succession. In any case, the several components may beadded in stages. Obviously mixtures of the individual components may beused.

In the preparation of the sulfamoyl indanes used in the presentinvention, it has been indicated that the sulfonyl chloride derivativeof the indanes may be reacted with ammonia to produce unsubstitutedsulfamoyl indanes or with monoalkyl amines to produce the alkylsubstituted sulfamoyl indanes. Amongst the monoalkyl amines which may beused to produce the latter class of compounds are methyl amine, ethylamine, propyl amine, butyl amine, amyl amine, hexyl amine, heptyl amine,octyl amine, nonyl amine, decyl amine, undecyl amine, dodecyl amine,tridecyl amine, tetradecyl amine, pentadecyl amine, hexadecyl amine,heptadecyl amine, octadecyl amine, nonadecyl amine, eicosyl amine andthe like. Although these amines may be used either singly or incombination With one another, it is preferred that they be used singly.The condensation products of the present invention may be used in aplurality of applications either alone or in combination with othernatural or synthetic resinous materials. Amongst the uses for the novelcondensation products of the present invention are in adhesives, coatingcompositions, printing inks, molding compositions, laminatingcompositions, potting compositions, textile treating compositionsincluding the treatment of natural and synthetic fibers and the fabricsderived therefrom including animal fibers as well as cellulosic fibers.Additionally, these novel condensation products may be used in thetreatment of cellulosic pulp in paper making operations, in thetreatment of non-fibrous regenerated cellulosic materials such as films,or they may be used in the treatment of leather for tanning purposes andthe like.

If it is desired, the novel condensation products of the presentinvention may be used in combination with other aminoplast resins suchas the aldehyde condensation products of such aldehyde-readablecompounds as urea, thiourea, ethylene diurea, and aminotriazines such asmelamine, benzoguanamine, formoguanarnine, acetoguanamine, 'ammeline,ammelide, the monodior trialkyl melamines such as2,4,6-triethyl-triarnino-1,3,5-triazine and the like. These condensationproducts may be unmodified or alcohol modified aldehyde reactionproducts. Still further, one may make use of alkyd resins prepared byreacting a polycarboxylic acid free of nonbenzenoid unsaturation with apolyhydric alcohol such as the glyptal resins either oil free or oilmodified, wherein the oil length may be either short oil, medium oil orlong oil alkyd resins. Still further, the novel condensation products ofthe present invention may be utilized in combination withketone-formaldehyde resins and the phenolics such as thephenol-formaldehyde resins or the epoxy type resins such as thosederived by reacting a halohydrin such as epichlorohydrin with a phenolsuch as his phenol and the like. Still further, the novel condensationproducts of the present invention may be utilized with such syntheticresins as the linear super polyamides, the linear super polyesters andthe like. The novel condensation products of the present invention mayadditionally be used in combination with natural resinous materials suchas the coumaIone-indene, gum damar, ester gum and the like.

The condensation products of the present invention are prepared byreacting the sulfamoyl indanes with aldehydes in a mol ratio varyingbetween about 1:1 and 1:4, respectively, and preferably 1:15 to 1:3.0,respectively for the unsubstituted sulfamoyl indaues. For thesubstituted sulfamoyl iudanes Where there are only two aldehyde reactivehydrogens on the nitrogen atoms, condensation products can be preparedby reacting said substituted sulfamoyl indanes with aldehydes in a molratio varying between about 1:1 and 1:2. If it is desired to insure thatas much aldehyde as possible reacts with the sulfamoyl indan, whethersubstituted or unsubstituted, an excess of aldehyde may be used.

The compositions of the present invention may be utilized with pigments,dyes, lubricants, promoters, cat- 45 alysts, accelerators, opacifiers,driers, and the like, when and as needed.

This application is a continuation-in-part of my earlier filedapplication, having the Serial No. 414,860, filed March 8, 1954,entitled Novel Compositions of Matter and Processes of Preparing theSame. More specifically, the parent application relates to a process forthe preparation of indan carboxylic acids and their use in thepreparation of alkyd resins.

I claim:

l. A process for the manufacture of condensation products comprisingcondensing an aldehyde and a compound having the formula:

RHNO S o-a R 1 so iNnru wherein R is a member selected from the groupconsisting of a halo group and an alkyl group, containing from 1 to 4carbon atoms, R is an alkyl group containing from 1 to 4 carbon atomsand R is a member selected from the group consisting of H and an alkylgroup containing 1 to 20 carbon atoms.

2. A process for the manufacture of condensation products comprisingcondensing formaldehyde and a compound having the formula:

RUINOzS SOzNHIR wherein R is a member selected from the group consistingof a halo group and an alkyl group containing from 1 to 4 carbon atoms,R is an alkyl group containing from 1 to 4 carbon atoms and R is amember selected from the group consisting of H and an alkyl groupcontaining 1 to 20 carbon atoms.

3. A process for the manufacture of condensation products comprisingreacting an aldehyde with 1-(4-methylsulfamoyl-phenyl)-1,1,3,6-tetramethyl-5-sulfarnoyl indan.

4. The reaction product produced by reacting an aldehyde with a compoundhaving the formula:

SOg'NHR wherein R is a member selected from the group consisting of ahalo group and an alkyl group containing from 1 to 4 carbon atoms, R isan alkyl group containing from 1 to 4 carbon atoms and R is a memberselected from the group consisting of H and an alkyl group containing 1to 20 carbon atoms.

5. The reaction product produced by reacting formaldehyde with acompound having the formula:

CH3 I-12 RHNOzS wherein R is a member selected from the group consistingof a halo group and an alkyl group containing from 1 to 4 carbon atoms,R is an alkyl group containing from 1 to 4 carbon atoms and R is amember selected from the group consisting of H and an alkyl groupcontaining 1 to 20 carbon atoms.

, 6. The reaction product produced by reacting formaldehyde with1-(4-methyl-sulfamoyl-phenyl)-1,1,3,6-tetramethyl-S-sulfamoyl indan.

' 7. .A process for the manufacture of condensation products comprisingcondensing an aldehyde with a compound /CH1 R F wherein R is a memberselected from the group consisting of a halo group and an alkyl groupcontaining from 1 to 4 carbon atoms, R is an alkyl group containing from1 to 4 carbon atoms and R is a member selected from the group consistingof H and an alkyl group containing 1 to 20 carbon atoms.

8. A process for the manufacture of condensation products comprisingcondensing formaldehyde with a compound containing at least onealcoholic hydroxy group and a compound having the formula:

R HN 028 SOiNIEIR wherein R is a member selected from the groupconsisting of a halo group and an alkyl group containing from 1 to 4carbon atoms, R is an alkyl group containing from 1 to 4 carbon atomsand R is a member selected from the group consisting of H and an alkylgroup containing 1 to 20 carbon atoms.

9. A process for the manufacture of condensation products comprisingcondensing an aldehyde with an aliphatic alcohol and1-(4-methyl-sulfamoyl-phenyl)-1,1,3,6-tetramethyl-S-sulfamoyl indan.

10. The reaction product produced by reacting an aldehyde with acompound containing at least one alcoholic hydroxy group and a compoundhaving the formula:

10 wherein R is a member selected from the group consisting of a halogroup and an alkyl group containing from 1 to 4 carbon atoms, R' is analkyl group containing from 1 to 4 carbon atoms and R is a memberselected from the group consisting of H and an alkyl group containing 1to 20 carbon atoms.

11. The reaction product produced by reacting formaldehyde with acompound containing at least one alcoholic hydroxy group and a compoundhaving the formula:

wherein R is a member selected from the group consisting of a halo groupand an alkyl group containing from 1 to 4 carbon atoms, R is an alkylgroup containing from 1 to 4 carbon atoms and R is a member selectedfrom the group consisting of H and an alkyl group containing 1 to 20carbon atoms.

12. The reaction product produced by reacting an aldehyde with acompound containing an alcoholic hydroxy group and1-(4-methyl-3-sulfarnoylphenyl)-1,1,3,6-tetramethyl-S-sulfamoyl indan.

13. The reaction product produced by reacting formaldehyde, methylalcohol and1-(4-methyl-3-sulfamoylphenyl)-1,1,3,6-tetramethyl-5-sulfamoyl indan.

14. The reaction product produced by reacting formaldehyde, butylalcohol and1-(4-methyl-3-sulfamoylphenyl)-1,1,3,6-tetramethyl-5-sulfamoyl indan.

15. A process for the manufacture of condensation products comprisingcondensing formaldehyde, methyl a1- cohol and1-(4-methyl-3-sulfamoylphenyl)-1,1,3,6-tetramethyl-S-sulfamoyl indan.

16. A process for the manufacture of condensation products comprisingcondensing formaldehyde, butyl alcohol and1-(4-methyl-3-sulfamoylphenyl)-1,1,3,6-tetramethyl- 5-sulfamoyl indan.

17. The reaction product produced by reacting formaldehyde and1-(4-sulfamoylphenyl)-1,3,3-trimethyl-6-sulfamoyl-indan.

18. The reaction product produced by reacting formaldehyde and1-(4-methyl-3-sulfamoylphenyl)-1,3-diethyl-3,6-dimethyl-5-sulfamoyl-indan.

19. The reaction product produced by reacting formaldehyde and1-(3-methyl-4-sulfamoylphenyl)-1,3,3,5-tetramethyl-6-sulfamoyl-indan.

20. The reaction product produced by reaction formaldehyde and1-[4-methyl-3-(propylsulfamoyl)-phenyl]1,3,3,6-tetramethyl-S-propylsulfamoyl-indan.

No references cited.

1. A PROCESS FOR THE MANUFACTURE OF CONDENSATION PRODUCTS COMPRISINGCONDENSING AN ALDEHYDE AND A COMPOUND HAVING THE FORMULA: